CAS 1887742-41-7 is an important pharmaceutical intermediate or active molecular fragment. It is not a bulk chemical or a general reagent.
The following is a comprehensive introduction to this compound:
1. Basic Information
· CAS Number: 1887742-41-7
· Common Name:
· (S)-2-((S)-4-Methyl-2,5-dioxoimidazolidin-4-yl)pent-4-ynoic acid (This is its systematic name and also the most common name)
· It may appear in some company catalogs in the form of a code, such as the structure of (S,S)-Methyl-DO3A-PNP-ester precursor.
· Molecular Formula: C₉H₁₀N₂O₄
· Molecular Weight: 210.19 g/mol
2. Chemical structure characteristics
From its systematic name, the key structural information of this molecule can be interpreted:
· Chiral Center: The two (S) in the name indicate that the molecule contains two specific chiral (three-dimensional) centers, meaning it has a definite three-dimensional structure. This stereoscopic chemical feature is crucial for its application in the medical field, as organisms typically have selective recognition for molecules of specific configurations.
· Core Skeleton: Contains an ethynylurea structural fragment. The ethynylurea ring (imidazolidine-2,4-dione) is a five-membered heterocyclic ring containing two amide bonds, commonly found in some molecules with biological activity.
· Functional Groups:
· Carboxylic Acid: Has a carboxyl group, allowing it to further react to form esters, amides, and other derivatives, facilitating connection with larger molecules.
· Alkyne: Contains a terminal acetylene group, which is a very reactive functional group. It can be efficiently and specifically connected with molecules containing azide groups through the copper-catalyzed acetylene-nitroso ring addition reaction in "click chemistry".
3. Main Uses and Importance
The main value of this compound lies in the fields of medicinal chemistry and chemical biology:
· Pharmaceutical intermediates: They are used as key building blocks for synthesizing more complex molecules. The imide ring in their structure is a common pharmacophore in many drug molecules and may have specific interactions with target proteins.
· **Linker or connector**: Due to its simultaneous presence of carboxylic acid and alkyne groups, it can act as a "bifunctional connector".
· The carboxylic acid end can be linked to a molecule through the formation of an amide bond.
· The alkyne end can be connected to another molecule containing a nitro group through click chemistry.
· Fragment-based drug discovery: These complex, chiral-centered small molecules are often used as "fragment libraries" for screening to search for lead compounds targeting specific disease targets.
· Specific application context: According to literature searches, this compound or its derivatives have been used in research for synthesizing macrocyclic chelators, such as as a precursor for (S,S)-MeDO3A. DO3A and its derivatives are important ligands for gadolinium contrast agents used in magnetic resonance imaging. Therefore, this compound may be related to the development of new MRI contrast agents.
4. Physical properties (typical values; specific values shall be determined based on actual measurements)
For such fine chemicals, their physical and chemical properties usually need to be determined through experiments, but they can be inferred based on their structures:
· Appearance: Likely to be a white to off-white solid powder.
· Solubility: Soluble in polar organic solvents such as dimethyl sulfoxide, N,N-dimethylformamide, methanol, etc. The solubility in water may vary depending on the pH value (the carboxylic acid groups become salted out and increase water solubility under alkaline conditions).
· Melting point: Expected to be high, possibly above 150°C.
5. Safety Information
· Lack of publicly available MSDS: As it is a research-grade fine chemical, there is no standardized public safety data sheet.
· General recommendations:
· It should be treated as a hazardous chemical.
· During operation, appropriate personal protective equipment should be worn, including laboratory coats, gloves, and goggles.
· Avoid inhaling dust and avoid contact with skin and eyes.
· The operation should be carried out in a well-ventilated area (such as a fume hood).
Summary
CAS 1887742-41-7 is a complex organic molecule with a specific stereoconfiguration and multiple functional groups. Its main value lies in being a key intermediate for the synthesis of more complex molecules (particularly those related to macrocyclic chelating agents and potential contrast agents). The ethynylurea ring, carboxyl group, and alkyne group in its structure jointly determine its significant applications in the fields of medicinal chemistry and bioconjugation.
United States